Apixaban

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Apixaban
Apixaban.svg
Systematic (IUPAC) name
1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5-dihydropyrazolo[5,4-c]pyridine-3-carboxamide
Clinical data
Trade names Eliquis
Licence data EMA:Link
Legal status
Routes Oral
Pharmacokinetic data
Bioavailability ca. 50%
Half-life 9–14 h
Excretion 75% biliary, 25% renally
Identifiers
CAS number 503612-47-3 YesY
ATC code B01A
PubChem CID 10182969
DrugBank DB07828
ChemSpider 8358471 YesY
UNII 3Z9Y7UWC1J YesY
KEGG D03213 YesY
ChEMBL CHEMBL231779 YesY
Chemical data
Formula C25H25N5O4 
Mol. mass 459.497 g/mol
 YesY (what is this?)  (verify)

Apixaban (BMS-562247-01, tradename Eliquis) is an anticoagulant for the treatment of venous thromboembolic events. It is a direct factor Xa inhibitor. Apixaban has been available in Europe since May 2012.[1] In the United States, it is undergoing phase III trials for the prevention of venous thromboembolism.[2] An FDA decision on apixaban which was expected on June 28, 2012 was delayed.[3][4] On August 21, 2014, Pfizer announced that Apixaban was now FDA approved for treatment and secondary prophylaxis of DVT and PE.[5] It is being developed in a joint venture by Pfizer and Bristol-Myers Squibb.[6][7]

Clinical trials[edit]

A 2007 trial showed that apixaban was equivalent to enoxaparin/open-label heparin in preventing thrombosis in patients who had undergone a knee replacement.[8] A 2010 trial showed that apixaban was superior to enoxaparin in preventing thrombosis in patients undergoing elective hip replacement surgery, with similar bleeding rates.[9][10]

A 2011 trial showed that in patients with atrial fibrillation who have failed or are not candidates for vitamin K antagonist therapy, apixaban, as compared with aspirin, reduced the risk of stroke or systemic embolism in patients experiencing atrial fibrillation by more than 50% (from 3.7% per year with aspirin to 1.6% per year with Apixaban). Difference in death rates did not reach statistical significance.[11] A 2011 trial showed that patients receiving apixaban after acute coronary syndrome experienced an increased rate of major bleeding episodes without a significant reduction in recurrent ischemic events.[12] For this reason, the trial was terminated early.

In a head-to-head study of apixaban versus warfarin,[13][14] apixaban met both its primary endpoint (“noninferiority” to warfarin in preventing strokes) and a key secondary endpoint (superior compared to warfarin in avoiding major bleeding).[15]

See also[edit]

References[edit]

  1. ^ "ELIQUIS® (apixaban) Approved In Europe For Preventing Venous Thromboembolism After Elective Hip Or Knee Replacement" (Press release). Pfizer. April 20, 2012. Retrieved 2012-05-29. 
  2. ^ Turpie AG (June 2007). "Oral, direct factor Xa inhibitors in development for the prevention and treatment of thromboembolic diseases". Arterioscler. Thromb. Vasc. Biol. 27 (6): 1238–47. doi:10.1161/ATVBAHA.107.139402. PMID 17379841. 
  3. ^ Huston, Larry (February 29, 2012). "Decision on Apixaban (Eliquis) Pushed Back By Three Months". Forbes. Retrieved 2012-05-29. 
  4. ^ Husten, Larry. "FDA Once Again Delays Approval Of Apixaban (Eliquis)". Forbes. Retrieved 17 July 2012. 
  5. ^ http://www.pfizer.com/news/press-release/press-release-detail/u_s_fda_approves_eliquis_apixaban_for_the_treatment_of_deep_vein_thrombosis_dvt_and_pulmonary_embolism_pe_and_for_the_reduction_in_the_risk_of_recurrent_dvt_and_pe_following_initial_therapy
  6. ^ "Bristol-Myers Squibb News Release 26 April 2007". Archived from the original on 11 September 2007. Retrieved 2007-09-15. 
  7. ^ Nainggolan, Lisa. "Apixaban better than European enoxaparin regimen for preventing VTE". Retrieved 2011-04-01. 
  8. ^ Lassen MR, Davidson BL, Gallus A, Pineo G, Ansell J, Deitchman D (2007). "The efficacy and safety of apixaban, an oral, direct factor Xa inhibitor, as thromboprophylaxis in patients following total knee replacement". J. Thromb. Haemost. 5 (12): 2368–75. doi:10.1111/j.1538-7836.2007.02764.x. PMID 17868430. 
  9. ^ Lassen MR, Gallus A, Raskob GE, Pineo G, Chen D, Ramirez LM, ADVANCE-3 Investigators (December 2010). "Apixaban versus enoxaparin for thromboprophylaxis after hip replacement". N. Engl. J. Med. 363 (26): 2487–98. doi:10.1056/NEJMoa1006885. PMID 21175312. 
  10. ^ Nainggolan L. "Apixaban better than European enoxaparin regimen for preventing VTE". theheart.org by WebMD. Retrieved 2011-04-01. 
  11. ^ "Apixaban in patients with atrial fibrillation". N. Engl. J. Med. 364 (9): 806–817. March 2011. doi:10.1056/NEJMoa1007432. PMID 21309657.  edit
  12. ^ Alexander JH, Lopes RD, James S, et al. (August 2011). "Apixaban with antiplatelet therapy after acute coronary syndrome". N. Engl. J. Med. 365 (8): 699–708. doi:10.1056/NEJMoa1105819. PMID 21780946. 
  13. ^ "Apixaban for the Prevention of Stroke in Subjects With Atrial Fibrillation (ARISTOTLE)". NCT00412984. ClinicalTrials.gov. Retrieved 2011-06-23. 
  14. ^ Granger CB, Alexander JH, McMurray JJV, et al. (August 2011). "Apixaban versus Warfarin in Patients with Atrial Fibrillation". New England Journal of Medicine 365. doi:10.1056/NEJMoa1107039. 
  15. ^ Husten L (2011-06-22). "ELIQUIS® (apixaban) Meets Primary and Key Secondary Endpoints in Phase 3 ARISTOTLE Study". CardioBrief. WordPress.com. Retrieved 2011-06-23.